Process of producing organic mercury compounds



' 1T0 Drawing.

-Pa'tented Feb. 25,1930 1 mx 'ENGELMANN, or

wnmmeron, DELAWARE, AssIGNoR T0 E.

NEMO'URS & COMPANY, OF-WILMINGTON, DELAWARE, CORPORATION OF DELE- WARE This invention relates to 'mercurized orgame compounds and more particularly to mercurlzed phenol compounds.

' The usual method of mercurizing organic compounds consists of heating organic derivatives -witha water or alcoholic solut on of organic or inorganic mercury salts. Vhen mercury salts having the tendency to form basic compounds are used, the common prac- +cH3coon coon: 1

Accordingto the above method 'one hal f of'tlie acetic acid is set free. Tlns acl d 1s practically lost. and increases the SOlHbIlIty of the mer'curiah'which necessitates an addit-ional step in the process torecover'the prod not from the mother liquor. Furthermore, according to the old method the process starts with a'complete solution of the mercury salt, the reaction runs very fast, and the mercury product resulting therefrom is very often formed as asticky and lumpy mass that is changed in the course of the reaction to a solid product, which is converted, after drying to a fine powder bygrinding. have now found that mercurized organic derivatives may be produced by a new process which consists in treating organic compounds in water, or in ,an organic Solvent, such as alcohol or the like, with mercury oxide and an amount'of acid less than that theoretically required to form the normal mercury'salt. Instead of a mixture of mercury oxide and acid, a basicsalt, or a normal salt in which the acid is partlyneutralized, can also be used. T his newprocess of preparing an organic mercury compound-has the advantage that the reaction is carried out in the presence of a very fine precipitate namely, the mercurytoxide or the basic salt. This pound in verysmall crystals which can be easily worked up to fine powders sultablefor Application filed A ril 15,

-nitrophenol,'or nitrocresol, and

causes the formation of the inercury com-" PROCESS OF ERODUCING ORGANIC MERCURY COMPOUNDS 1 1927. Seria1uNo.184,186. f A t The product produced according to my process consists of fine crystalline material and does not require grinding to convert it to a powder.- The following example is given I. DU PON'I. DE

as an illustration of the,'product produced according to my process but it is to be understood tlllt tllls in no Way is to be taken as a limitation of my lnventlon.

. I 4J5 parts of mercury oxide are suspended in 300 parts of water; 14 parts of glacial M acetic acid-are added, and the entire charge heated to 85 C. Only a partvof the oxide goes into solution. 17.5 parts of 0mm,

' ,chlorphenol are added over a period of about 2 hours. The indicated temperature is then maintained for one hour longer. The reaction is. finished when the precipitated mercury compound is entirely soluble in diluted sodium hydrate solution. The charge isthen filtered and dried. The mercury compound thus formed isa mixture of monoand d1- lercurized chlorphenol with about 63% of mercury. It is insoluble in water, very slightly soluble in alcohol, insoluble in benzol, ether and othe'rorganic solvents. uble in sodium or potassium hydrate solutions. It is stable to sulfuric acid, nitricacid,

etc. Boiling hydrochloric acid decomposes it to chlorphenol and mercury bichloride.

The acetic acid in this reaction can be su'bstituted by .any other acids whose mercury salts are suitable for mercurizing organic compounds. The chlorphenol may be sub stituted by other phenols such tfor e. g as ganic compounds which are qualified to react with mercury salt fto'form the organic,v metal derivatives. 1 I

This process may be applied either to pure It is easily so 75 organic compounds or to mixtures of isomers such as the orthoand para-chlorphenolgor to such materials as the crude nitroor chlorphenols.

As many apparently. widely different em;

bodiments in this invention may be made withoutdeparting from the spirit thereof, it is to be understood that I do not limit myself to the foregoing example or description except as" indicated ,in the following patent claims;

I'clain'i: 1 g 1. The process'of producing a mercurized phenol which comprises reacting upon a phenolic compound with basicmercuricacetate.

2. The process of producing a mercurlzed phenol which comprises reacting. upon aphenolic compound with mercury oxide in the presence of an-amount of acetic acidlessthan that required to form the normal mercury salt. Q '3. The process of producing a mercurized chlorphenol which'comprises reacting upon a chlorphenol, with basic mercuric acetate. The process of producing a mercurized chlor henol which comprises reacting upon a chl drphenol with mercury oxide in the presence of an amount of acetic acid less 'thanthat required to form the normal mercury salt. Y a

2g 5. The process of producing ortho-clilorphenol mercury which comprises reacting upon ortho-chlorphenol with basic mercuric acetate. p

6. The process of producing ortho-chlorphenol mercury which comprises reacting upon ortho-chlorphenol with mercury oxide in the presence of an amount ofacetic acid less than that required to form "the normal mercury salt. it I 7 s so, 7. The process of producing mercurized chlorphenol compounds which comprises rep acting upon a mixture of ortho-and para chlorphenol with basic mercuric acetate; v 8. The process of producing mercurized ehlorphenol compounds which comprises reacting upon a mixture of orthoand parachlorphenol with mercuryoxide in the presence of an amount of aceticacid less than that required to form thefnormal mercury 40 salt. '9. The 'process of producing me'rcurized chlorphenol compounds which comprises reacting upon a mixture of .crude orthoand para-chlorphenol with'mercury oxide in the presence of basic mercuric acetate. 10. The process of producing mercurized chlorphenol compounds which: comprises reacting upon. a, crude mixture of orthoand ,.para-chlorphenol with mercury oxide in the presence of van amount of acetic acid less .than that required to form the normal mercury salt.v I r v 11. The" processof producing mercurized chlorphenol compounds which comprises reacting upon crude chlorinated phenol with mercury oxide in the presence of a qalnount of acetic acid less than that required to form the. normal mercury salt.

In. testimony whereof I afiix my signature. o

MAX ENGELMANN. 

